The object of the authors’ research is the modern society, in which digitalization initiates the endless change of situations derived from the development of the information technology environment. Digitalization is transforming systemic social processes, local practices, and such a strategically important area as education, which is most sensitive to a state of uncertainty. Since uncertainty causes existential risks, the need for an anthropological approach to the analysis of everyday life arises in the study of the risk-generating aspect of education. The authors find it promising to use the potential of riskological concepts to analyze the dynamics of modern education. Attention is focused on the institutional and value dimension; the important role of situationality is determined. The authors identify the risks of individualization, rationalization and technological development of education as situations characterized by instability, carrying the potential of both threats and dangers, and prospects and opportunities. This confirms the contradictory nature of the inevitable changes taking place in education, which at the same time bring a new type of rationality to social development. Modern realities are transforming the system of established institutions, where the institution of education begins to play a leading role, which involves new prospects and risks at the same time.